The present invention relates to a method for the synthetic preparation of an alkynyl halide compound and further relates to a method for the preparation of an alkenyl acetate compound which can be derived from the alkynyl halide compound as an intermediate. In particular, the invention relates to a method for the preparation of 7,11-hexadecadinyl acetate known as a sexual pheromone compound of pink bolloworm.
As is well known, a specific compound is attractive to a specific species of insects of a sex even with an extremely small amount and such a compound known by the name of a sexual pheromone compound presents a promising means for the extermination of noxious insects in the fields. It is also known that the sexual pheromone compounds of several important noxious insects in the agriculture and forestry chemically belong to a class of alkenyl acetate compounds. For example, the sexual pheromone compound of pink bolloworm is known to be the above mentioned 7,11-hexadecadienyl acetate.
Accordingly, the inventors have conducted to develop a novel and improved method for the synthetic preparation of such alkenyl acetate compounds and arrived at an idea that the desired alkenyl acetate compound may be advantageously prepared from an alkynyl halide compound as an intermediate.
Unfortunately, there have been known no industrially advantageous method for the synthesis of such an alkynyl halide compound or an alkenyl acetate compound such as 7,11-hexadecadienyl acetate to present a great obstacle to the practical application of the sexual pheromone compounds for the extermination of the noxious insects.